The present invention relates to 1,3,6-dioxazocan-2-ones and antimicrobial polycarbonates formed therefrom by organocatalyzed ring opening polymerization, and more specifically to antimicrobial cationic polycarbonates comprising a quaternary nitrogen in the polycarbonate backbone.
Current ring opening polymerizations of cyclic carbonates are limited by the lack of main chain functionality in the polycarbonate other than the carbonate functionality. The incorporation of heteroatoms (e.g., nitrogen) in the polymer backbone is hampered by monomer instability. Heteroatom incorporation other than the carbonate oxygens within a 7-membered ring or smaller ring monomer produces an unstable species (e.g., acetals, hemiaminals, and thioacetals for 6-membered and 7-membered rings, and peroxides and N-oxides for 5-membered rings).
Cyclic carbonate monomers comprising a ring heteroatom in addition to the carbonate oxygens are needed, in particular those comprising a ring nitrogen. Also needed are methods of ring opening polymerizations that produce polymers bearing a heteroatom other than carbonate oxygens.